Oak Bluffs Vacation Rentals

Oak Bluffs is a beautiful peninsula on the north eastern coast of Martha’s Vineyard that is bordered by Nantucket Sound. Renting a vacation home in Oak Bluffs gives you so many options. Our list of vacations rentals include luxury waterfront properties with exceptional views of the sound and quaint Victorian homes that allow you to glimpse deeply into Martha’s Vineyard’s historic past. Vacationing in Oak Bluffs is like taking a trip back in time. Ocean air and private beaches make you feel as though you have Martha’s Vineyard all to yourself.

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Lovely New 3 Bedroom, 3.5 Bath Home, 15 min walk to Oak Bluffs Center, Inkwell Beach and Town Beach, Sleeps 8, 3 Bedrooms, Plus Loft, 3.5 Baths

This stylish contemporary retreat is ideally located in a lovely, peaceful Oak Bluffs neighborhood, just a 10–15 minute stroll to the village center, parks, Inkwell Beach, Oak Bluffs Town Beach, and...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$5,250 - $13,960
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$9,760
6
7
8
9
10
11
12
$9,760
13
14
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19
$9,760
20
21
22
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24
25
26
$9,760
27
28
29
30
 $9,760
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,760
4
5
6
7
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9
10
$10,460
11
12
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17
$10,460
18
19
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21
22
23
24
$10,460
25
26
27
28
29
30
31
$10,460
August 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
6
7
$13,960
8
9
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$13,960
15
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21
$13,960
22
23
24
25
26
27
28
$13,960
29
30
31
 $13,960
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$13,960
5
6
7
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10
11
$9,060
12
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18
$6,650
19
20
21
22
23
24
25
$6,650
26
27
28
29
30
 $6,650
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

2026, Owner offers 10% discount off rental rate - May, June, July weeks for 7 night stay or longer. 

 

3 night minimum stay required, May, June to last week, September 5 on &, October. 

 

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CORAG

Inquire
Property Details
Lovely, Newly Updated Oak Bluffs Home. Multiple Indoor/Outdoor Living/Lounge Areas, Sleeps 8, 10/15 minute Walk to the Vilage Center.

Note: All photos are virtually staged photos by the owner, all new furnishings will be arriving throughout the winter months. 

Welcome to Noble House, a beautifully updated home nestled in a charming neighborhood just...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
3
Baths: 
2
Price Range:
$4,500 - $13,120
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,250
6
7
8
9
10
11
12
$6,880
13
14
15
16
17
18
19
$7,500
20
21
22
23
24
25
26
$8,440
27
28
29
30
 $10,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$10,000
4
5
6
7
8
9
10
$11,880
11
12
13
14
15
16
17
$10,000
18
19
20
21
22
23
24
$10,620
25
26
27
28
29
30
31
$11,130
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$13,120
8
9
10
11
12
13
14
$13,120
15
16
17
18
19
20
21
$12,130
22
23
24
25
26
27
28
$11,560
29
30
31
 $9,060
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,060
5
6
7
8
9
10
11
$8,750
12
13
14
15
16
17
18
$7,500
19
20
21
22
23
24
25
$7,190
26
27
28
29
30
 $6,880
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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BAKE7

Inquire
Property Details
Waterview, Walk to the Beach and Town Center, Impeccably Maintained 4 bedroom Home set in the Heart of Oak Bluffs.

This restored historic J.A. Norton Main and Guest Suite Quarters seamlessly blends 1870s character with the modern comforts today’s travelers appreciate. Nestled in a peaceful  Oak Bluffs neighborhood, the property is just...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,400 - $13,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,400
6
7
8
9
10
11
12
$4,400
13
14
15
16
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18
19
$4,900
20
21
22
23
24
25
26
$4,900
27
28
29
30
 $6,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$6,000
4
5
6
7
8
9
10
$8,800
11
12
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$8,800
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19
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21
22
23
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$8,900
25
26
27
28
29
30
31
$9,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
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5
6
7
$12,000
8
9
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$12,000
15
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$13,000
22
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27
28
$13,000
29
30
31
 $8,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,500
5
6
7
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11
$5,600
12
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$5,600
19
20
21
22
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24
25
$5,600
26
27
28
29
30
 $5,600
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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MILTD

Inquire
Property Details
Perfect in Town Location. Just 1 to 2 blocks to Beach, Town Center & Harbor Area, Walk to and from the Ferry

Centrally located in the heart of Oak Bluffs, walk 1-2 blocks to the beach, public tennis courts, and town & harbor areas. This wonderful large home has a large wrap-around porch for relaxing, 7...Read more

Location: 
Oak Bluffs
Sleeps: 
14
Bedrooms: 
7
Baths: 
3
Price Range:
$8,500 - $12,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$9,500
6
7
8
9
10
11
12
$9,500
13
14
15
16
17
18
19
$9,500
20
21
22
23
24
25
26
$9,500
27
28
29
30
 $13,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$13,500
4
5
6
7
8
9
10
$13,500
11
12
13
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$13,500
18
19
20
21
22
23
24
$13,500
25
26
27
28
29
30
31
$13,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$13,500
8
9
10
11
12
13
14
$13,500
15
16
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18
19
20
21
$13,500
22
23
24
25
26
27
28
$13,500
29
30
31
 $12,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$12,500
5
6
7
8
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10
11
$12,500
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13
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18
$12,500
19
20
21
22
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24
25
$12,500
26
27
28
29
30
 $12,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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PIN15

Inquire
Property Details
Beautiful Oak Bluffs Home, Screened Porch & Open Porch, Association Tennis Courts, 4 bedrooms, 3.5 baths, Ideally Located just 2 miles to Town and Beach

Spacious contemporary home nestled in the lovely community of homes Meadow View Farms just on the outskirts of Oak Bluffs and 2 miles to town center and Oak Bluffs beaches....Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$8,000 - $12,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
$9,000
27
28
29
30
 $9,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,000
4
5
6
7
8
9
10
$9,000
11
12
13
14
15
16
17
$9,000
18
19
20
21
22
23
24
$12,500
25
26
27
28
29
30
31
$12,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$12,500
8
9
10
11
12
13
14
$12,500
15
16
17
18
19
20
21
$12,500
22
23
24
25
26
27
28
$12,500
29
30
31
 $12,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$12,500
5
6
7
8
9
10
11
$12,500
12
13
14
15
16
17
18
$8,500
19
20
21
22
23
24
25
$8,500
26
27
28
29
30
 $8,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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JOSEJ

Inquire
Property Details
Exquisite Coastal Style Home, Pool, Patio, Landscaped Yard! 10 minute walk to Oak Bluffs Center, Luxury Interior, 3 bedrooms, 4 baths, Multiple Living Spaces

This newly constructed, luxurious home offers the perfect blend of comfort, style, and convenience. Featuring a heated 16 x 32' pool with varying depths of 3 to 8 feet, a...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,000 - $12,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,000
6
7
8
9
10
11
12
$6,000
13
14
15
16
17
18
19
$6,000
20
21
22
23
24
25
26
$6,000
27
28
29
30
 $12,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$12,000
4
5
6
7
8
9
10
$12,000
11
12
13
14
15
16
17
$12,000
18
19
20
21
22
23
24
$12,000
25
26
27
28
29
30
31
$12,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$14,500
8
9
10
11
12
13
14
$14,500
15
16
17
18
19
20
21
$14,500
22
23
24
25
26
27
28
$11,500
29
30
31
 $11,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,500
5
6
7
8
9
10
11
$7,500
12
13
14
15
16
17
18
$6,000
19
20
21
22
23
24
25
$6,000
26
27
28
29
30
 $6,000
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

Pool Heated to  81 degrees included in rental rate last Sat in June to first Sat in September. Pool Depth 3 feet to 8 Feet 

Pool Heated to 81 degrees June and September weeks additional $275 per week  

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ROSKH

Inquire
Property Details
East Chop Classic Waterfront Home, Private Dock, Mooring Available, Spectacular Sunsets, For 2027 this Home is Under the code MUCCJ

Experience refined coastal living at this exceptional cottage- style waterfront retreat in the coveted East Chop area of Oak Bluffs. 

This idyllic waterfront summer sanctuary is poised to create cherished...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$8,000 - $12,000
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSa
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August 2027
SuMoTuWeThFrSa
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September 2027
SuMoTuWeThFrSa
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21
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25
26
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28
29
30
 
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

Owner reduced rate for weeks 8/15 & 8/22 - see calendar for adjusted rates

This property is under a new code for the 2027 season.  Please see MUCCJ

 

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MANUC

Inquire
Property Details
Hart Haven, Spacious Contemporary Colonial, Private Association Beach .8 mi from house, Private Association Tennis, 5 min walk from house

Located in the desirable enclave of homes known as Hart Haven just on the outskirts of Oak Bluffs Center, rental guests will surely enjoy this beautifully maintained home bordered by...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$10,000 - $12,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$10,000
6
7
8
9
10
11
12
$10,000
13
14
15
16
17
18
19
$10,000
20
21
22
23
24
25
26
$10,000
27
28
29
30
 $11,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$11,000
4
5
6
7
8
9
10
$11,000
11
12
13
14
15
16
17
$11,000
18
19
20
21
22
23
24
$11,000
25
26
27
28
29
30
31
$11,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$12,000
8
9
10
11
12
13
14
$12,000
15
16
17
18
19
20
21
$12,000
22
23
24
25
26
27
28
$12,000
29
30
31
 $11,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,000
5
6
7
8
9
10
11
$10,000
12
13
14
15
16
17
18
$10,000
19
20
21
22
23
24
25
$10,000
26
27
28
29
30
 $10,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
Add Favorite
 
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POWDA

Inquire
Property Details
Beautiful Newly Updated Oak Bluffs Home, Nestled on a Large Landscaped Lot in a Quiet Enclave of Homes. 4 Bedrooms. 4.5 Baths

Step inside to discover a welcoming interior, highlighted by a sunroom featuring comfortable seating around the TV. The open first-floor plan seamlessly integrates the main family room complete with a media...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,000 - $12,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,000
6
7
8
9
10
11
12
$6,500
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$7,500
27
28
29
30
 $8,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$8,500
4
5
6
7
8
9
10
$8,500
11
12
13
14
15
16
17
$8,500
18
19
20
21
22
23
24
$9,000
25
26
27
28
29
30
31
$9,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$12,000
8
9
10
11
12
13
14
$12,000
15
16
17
18
19
20
21
$11,500
22
23
24
25
26
27
28
$9,000
29
30
31
 $7,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,000
5
6
7
8
9
10
11
$6,000
12
13
14
15
16
17
18
$6,000
19
20
21
22
23
24
25
$6,000
26
27
28
29
30
 $6,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
Add Favorite
 
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PEMBT

Inquire
Property Details
Oak Bluffs Vacation Retreat – Exceptional Craftsmanship, Thoughtful Design & Unmatched Comfort, Sleep 8

Custom crafted with extraordinary attention to detail, quality, and comfort, this stunning Oak Bluffs vacation home offers an exceptional island getaway. Nestled in a peaceful residential neighborhood just two miles...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$4,500 - $12,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$5,500
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$7,500
27
28
29
30
 $9,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,000
4
5
6
7
8
9
10
$9,000
11
12
13
14
15
16
17
$9,000
18
19
20
21
22
23
24
$9,000
25
26
27
28
29
30
31
$11,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$12,000
8
9
10
11
12
13
14
$12,000
15
16
17
18
19
20
21
$12,000
22
23
24
25
26
27
28
$10,000
29
30
31
 $9,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,000
5
6
7
8
9
10
11
$7,500
12
13
14
15
16
17
18
$6,500
19
20
21
22
23
24
25
$5,500
26
27
28
29
30
 $5,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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ROCHA

Inquire
Property Details
Bridle Path House, Quiet Lovely Neighborhood, Porch and Deck Areas, Large Yard, Central Location to all 3 Down Island Towns and Beaches

Lovely 3 bedroom 3 bath home sleeps 8, bordered by a large landscaped yard. The exterior features a shady wrap-around porch with rockers, a perfect place to relax, read a book,  and enjoy...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$8,000 - $11,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,000
6
7
8
9
10
11
12
$8,000
13
14
15
16
17
18
19
$8,000
20
21
22
23
24
25
26
$8,000
27
28
29
30
 $9,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,800
4
5
6
7
8
9
10
$9,800
11
12
13
14
15
16
17
$9,800
18
19
20
21
22
23
24
$9,800
25
26
27
28
29
30
31
$9,800
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
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$9,800
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9
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$10,500
15
16
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$11,500
22
23
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$9,800
29
30
31
 $9,800
September 2027
SuMoTuWeThFrSaWeek
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2
3
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$9,800
5
6
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$9,000
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$9,000
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$9,000
26
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29
30
 $8,000
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
Add Favorite
 
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WEI81

Inquire
Property Details
Lovely Oak Bluffs Escape, 3 Bedrooms in Main House, 2 Bedrooms over Garage, 3.5 Baths Multiple Living Spaces, Walk to Oak Bluffs Center, 1 Mile

Nestled on a tranquil cul-de-sac in the heart of Oak Bluffs, this meticulously renovated Modern Colonial offers a special Martha's Vineyard experience. Thoughtfully reimagined in 2025, the property encompasses a...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$7,000 - $10,000
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSa
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August 2027
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September 2027
SuMoTuWeThFrSa
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Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
Add Favorite
 
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PRIAN

Inquire
Property Details
Beautiful Upscale Contemporary Home, Designer Details Throughout, 4 Bedrooms, 4.5 Baths, Muliple Living Areas

Discover this stunning tri-level vacation home nestled in a peaceful community just on the outskirts of Oak Bluffs and minutes away from Oak Bluffs center, Edgartown Village, downtown Vineyard Haven, and several...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
4
Price Range:
$8,300 - $9,900
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
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9
10
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12
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14
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21
22
23
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25
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29
30
 $8,300
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$8,300
4
5
6
7
8
9
10
$8,500
11
12
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$8,500
18
19
20
21
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23
24
$8,750
25
26
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30
31
$8,750
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
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$9,900
8
9
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$9,900
15
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25
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$8,750
29
30
31
 
September 2027
SuMoTuWeThFrSa
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Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
Add Favorite
 
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VANA2

Inquire
Property Details
Charming , Modern In-Town Oak Bluffs Vacation Home. Walk to Town, Parks, Beach. 4 Bedrooms, Sleeps 8, 3 Baths

This charming Oak Bluffs home is tucked away in a peaceful neighborhood, yet conveniently located just a 10-minute walk to the heart of town, the harbor, and the beach. Meticulously...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$5,000 - $9,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
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10
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$5,000
20
21
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23
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$5,000
27
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29
30
 $5,000
July 2027
SuMoTuWeThFrSaWeek
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2
3
$5,000
4
5
6
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8
9
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$6,500
11
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$6,000
18
19
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$6,500
25
26
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$7,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
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$9,500
8
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$9,500
15
16
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18
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$9,500
22
23
24
25
26
27
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$6,500
29
30
31
 $5,000
September 2027
SuMoTuWeThFrSaWeek
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2
3
4
$5,000
5
6
7
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10
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$5,000
12
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21
22
23
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25
26
27
28
29
30
 $4,500
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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CURRM

Inquire
Property Details
Outstanding Designer Home, 15 Min Walk to Oak Bluffs Center, 4 Bedrooms each en suite with TV, Occupancy Limit 9

Stylish Dreamy Home on Dreamer's Way, less than a mile from the town center and beach area! The owners have left nothing out in the way of design and comfort in...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
4
Baths: 
4
Price Range:
$3,500 - $9,400
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$6,500
6
7
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$7,100
13
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$7,700
20
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$8,400
27
28
29
30
 $9,000
July 2027
SuMoTuWeThFrSaWeek
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2
3
$9,000
4
5
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9
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$9,000
11
12
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$9,400
18
19
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23
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$9,700
25
26
27
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29
30
31
$9,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
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$11,200
8
9
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12
13
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$11,700
15
16
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18
19
20
21
$11,200
22
23
24
25
26
27
28
$10,000
29
30
31
 $8,400
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,400
5
6
7
8
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10
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$7,000
12
13
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$6,000
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
 $4,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Owner ACCEPTS 3 NIGHT MINIMUM STAYS, MEMORIAL DAY WEEKEND TO JUNE 16TH, AND SEPT 7TH TO THE END OF OCTOBER.

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